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peri Annelation of Perimidines in Reactions with 1,3-Dicarbonyl Compounds*

Chemistry of Heterocyclic Compounds volume 50, pages 1298–1304 (2014)Cite this article

An Erratum to this article was published on 01 May 2016

A new approach to 1,3-diazapyrenes via peri annelation of perimidines with 1,3-dicarbonyl compounds is developed. It is demonstrated that this method has a number of advantages compared to a previously reported procedure employing chalcones as electrophilic components. The new method can be used for efficient double peri annelation of biperimidines with 1,3-dicarbonyl compounds affording 2,2′-bi-1,3-diazapyrenes.

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References

  1. C. Wang, H. Dong, W. Hu, Y. Liu, and D. Zhu, Chem. Rev., 112, 2208 (2012).

    Article  CAS  Google Scholar 

  2. J. E. Anthony, Angew. Chem., Int. Ed., 47, 452 (2008).

    Article  CAS  Google Scholar 

  3. B. C. Thompson and J. M. J. Fréchet, Angew. Chem., Int. Ed., 47, 58 (2008).

    Article  CAS  Google Scholar 

  4. S. Geib, S. C. Martens, U. Zschieschang, F. Lombeck, H. Wadepohl, H. Klauk, and L. H. Gade, J. Org. Chem., 77, 6107 (2012).

    Article  CAS  Google Scholar 

  5. S. C. Martens, U. Zschieschang, H. Wadepohl, H. Klauk, and L. H. Gade, Chem.-Eur. J., 18, 3498 (2012).

    Article  CAS  Google Scholar 

  6. I. Piantanida, V. Tomišić, and M. Zinić, J. Chem. Soc., Perkin Trans. 2, 375 (2000).

    Article  Google Scholar 

  7. V. Balzani, A. Credi, S. J. Langford, F. M. Raymo, J. F. Stoddart, and M. Venturi, J. Am. Chem. Soc., 122, 3542 (2000).

    Article  CAS  Google Scholar 

  8. P. J. Stang, B. Olenyuk, J. Fan, and A. M. Arif, Organometallics, 15, 904 (1996).

    Article  CAS  Google Scholar 

  9. P. J. Stang, D. H. Cao, S. Saito, and A. M. Arif, J. Am. Chem. Soc., 117, 6273 (1995).

    Article  CAS  Google Scholar 

  10. A. V. Aksenov, A. S. Lyakhovnenko, N. A. Aksenov, and I. V. Aksenova, Rev. J. Chem., 2, 208 (2012). [Obzorn. Zh. Khim., 2, 242 (2012).]

    Article  Google Scholar 

  11. A. V. Aksenov, M. Kh. Magamadova, D. A. Lobach, I. V. Aksenova, and S. N. Ovcharov, Chem. Heterocycl. Compd., 48, 1267 (2012). [Khim. Geterocycl. Soedin., 1360 (2012).]

    Article  CAS  Google Scholar 

  12. A. V. Aksenov and I. V. Aksenova, Chem. Heterocycl. Compd., 45, 130 (2009). [Khim. Geterocycl. Soedin., 167 (2009).]

    Article  CAS  Google Scholar 

  13. S. V. Shcherbakov, D. A. Lobach, and A. V. Aksenov, Chem. Heterocycl. Compd., 50, 300 (2014). [Khim. Geterocycl. Soedin., 327 (2014).]

    Article  CAS  Google Scholar 

  14. A. V. Aksenov, A. S. Lyakhovnenko, I. V. Aksenova, and O. N. Nadein, Tetrahedron Lett., 49, 1808 (2008).

    Article  CAS  Google Scholar 

  15. A. V. Aksenov, I. V. Aksenova, A. S. Lyakhovnenko, and D. A. Lobach, Russ. Chem. Bull., 58, 859 (2009). [Izv. Akad. Nauk, Ser. Khim., 841 (2009).]

    Article  CAS  Google Scholar 

  16. I. V. Borovlev, A. V. Aksenov, and A. F. Pozharskii, Chem. Heterocycl. Compd., 33, 1367 (1997). [Khim. Geterocycl. Soedin., 1579 (1997).]

    Article  CAS  Google Scholar 

  17. I. V. Borovlev, O. P. Demidov, and A. F. Pozharskii, Chem. Heterocycl. Compd., 38, 968 (2002). [Khim. Geterocycl. Soedin., 1109 (2002).]

    Article  CAS  Google Scholar 

  18. A. F. Pozharskii, V. A. Anisimova, and E. B. Tsupak, Practical Heterocyclic Chemistry [in Russian], Rostov-on-Don (1988), p. 87.

  19. V. Paragamian, M. B. Baker, B. M. Puma, and J. Reale, J. Heterocycl. Chem., 5, 591 (1968).

    Article  CAS  Google Scholar 

  20. F. Sachs, Justus Liebigs Ann. Chem., 365, 53 (1909).

    Article  CAS  Google Scholar 

Download references

This work was financially supported by the Russian Scientific Fund (grant 14-23-00068).

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Authors and Affiliations

  1. North Caucasus Federal University, 1a Pushkina St., Stavropol, 355009, Russia

    A. V. Aksenov, M. H. Magamadova, D. A. Lobach, I. V. Aksenova & I. V. Malikova

  2. Department of Chemistry, University of Kansas, 1255 Wescoe Hall Drive, Lawrence, KS, 66049, USA

    M. Rubin

Authors
  1. A. V. Aksenov
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  2. M. H. Magamadova
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  3. D. A. Lobach
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  4. I. V. Aksenova
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  5. I. V. Malikova
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  6. M. Rubin
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Correspondence to A. V. Aksenov.

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*Dedicated to Academician Yurii Nikolaevich Bubnov on the occasion of his 80th birthday and in memory of working together.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1408-1415, September, 2014.

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Aksenov, A.V., Magamadova, M.H., Lobach, D.A. et al. peri Annelation of Perimidines in Reactions with 1,3-Dicarbonyl Compounds*. Chem Heterocycl Comp 50, 1298–1304 (2014). https://doi.org/10.1007/s10593-014-1592-2

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  • DOI: https://doi.org/10.1007/s10593-014-1592-2

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